After celebrating the girl's birthday last night, it's clear that we've got some chemistry going on. The boyfriend is kind of a jerk, who spouts inconsiderate comments, doesn't treat the girl even on her birthday, and has no idea of chivalry. Sometimes, when I go out with the guy in question, i'm worried that he'll offend someone and get us both into a fight.

On the other hand, the girl appreciates my compliments and says things to the boyfriend like "You never say those things to me!"

He's the kind of person who has no real plans for his life and makes spontaneous ambitions for law school. Both don't have jobs. I've got a job and could support the girl until she finds a job of her own. He's got a sub 3.0 G.P.A and is somewhat of an alcoholic. I'm worried that his influence is making the girl a bit of an alcoholic as well.

I'm torn. The friend is a good friend, but not a friend I would probably want to be around for life. The girl is probably the only person who I've had a sustainable connection with. Both of them joke around by saying that I'm contending for best man, but the guy said that he's waiting to propose in graduate school (I assume in 2011?).

My plan so far is to be available and wait it out. What would the AskMeFi community suggest?

If you are the kind of guy that likes all kinds of unnecessary and potentially violent drama in his life, I say go for it. Otherwise, I wouldn't touch this with a 10 foot stick.posted by chillmost at 5:07 AM on July 29, 2010 [25 favorites]

Excitedly getting your best friend's girlfriend's number is what falls under "no idea of chivalry."

Why not remove yourself from this situation entirely? It doesn't sound like you like your best friend much at all, and, as for the girl -- she has a boyfriend already.posted by kmennie at 5:07 AM on July 29, 2010 [22 favorites]

What would the AskMeFi community suggest?

Be available and wait it out. If the relationship is a bad one and not going to work in the long run, doing anything else is asking for trouble.posted by aheckler at 5:10 AM on July 29, 2010 [5 favorites]

I think you should back off and not spend much time with either of them for a while. If he's really such a sleaze maybe she'll come to her sense and you can get a shot but hanging around pining for the girl is just going to make you miserable and induce drama.

It seems like you want to be the white knight who saves her from some douche. Hard as it may be to believe she probably has reasons for being with him, respect her choices.posted by ghharr at 5:10 AM on July 29, 2010 [1 favorite]

You think you're somehow entitled to "get" your "friend's" girlfriend because you'd pay for dinner and your GPA is higher than his? I'm sorry, but no.

If you look down on this guy so much, how is it that you respect the girl so much? They sound pretty similar. They both don't have jobs. They're both not too able to pay for things. They both strike you as sort-of alcoholics. You have a double-standard because she's the one you want to have sex with.

It's easy to be critical of the boyfriend when you'd rather you were the boyfriend, but you have no idea what she sees in him. Can't you give her enough credit to realize she sees something in him?

Beyond passively waiting around in case they do break up (and not thinking about it too much in the meantime), don't bother acting on this. It's just a recipe for drama. You've never had a "sustainable connection" with anyone else before? OK, but that doesn't mean she's your only opportunity to have a sustainable connection with someone.posted by Jaltcoh at 5:12 AM on July 29, 2010 [81 favorites]

On the other hand, the girl appreciates my compliments and says things to the boyfriend like "You never say those things to me!"

The operative thing to realize about this statement is she wants these things from him, not you. That's an indication of who she wants to be dating.

I have also managed to get the girl's cell phone number last night.

What does "managed" mean? Did she give it to you or did you find a way to sneakily get it? If it's the latter, your friend isn't the only one who is kind of a jerk. Friends don't "manage" to get their friends' partner's cell numbers and they certainly don't portray it like some kind of conquest.posted by Hiker at 5:19 AM on July 29, 2010 [2 favorites]

For the record, she gave me the number. I did not ask for it.posted by BearPaws at 5:21 AM on July 29, 2010

Perhaps I'm being too judgmental, but how can you seriously describe your best friend in such abhorrently negative terms? If he's truly your best friend and these attributes are troubling you, then you'd do your best to help him grow as a person... rather than acting like a hyena and waiting for the best opportunity to steal his girlfriend's affections.

You certainly aren't coming off as a nice guy. Your ego is troubling as well. Congratulations for having a job and 3.0+ GPA. Even if you're just out of school that's incredibly naive.posted by Raze2k at 5:23 AM on July 29, 2010 [5 favorites]

Get drunk with them and stay on their couch. Convince her to stay up and watch the Wedding Singer with you (with a blanket). Get the girl.posted by doublehappy at 5:24 AM on July 29, 2010 [3 favorites]

This is simple: You call her up, and ask her out on a date. Make sure you are clear that this is a date by saying something like, "Would you like to go out on a date with me, on DATE at TIME to ACTIVITY OR PLACE?"

Naturally she has a choice in who she dates, and who she talks to about this conversation.posted by Houstonian at 5:24 AM on July 29, 2010 [3 favorites]

The girl is probably the only person who I've had a sustainable connection with

She is not your one and only true love - trust me, such a thing does not exist.
To make a long term relationship work requires effort, not some magical Hollywood love potion.posted by Flood at 5:26 AM on July 29, 2010 [1 favorite]

For the record, she gave me the number. I did not ask for it.

Did she give it to you, as in "call me, wink?" or did she give it to you for a specific purpose?

That's going to say a lot about what you should use it for.posted by Hiker at 5:29 AM on July 29, 2010

She's a friend of yours by the sounds of it. What would I tell my friend to do in this situation? Leave the dick of a boyfriend. If you want to make her happy, then be a friend.posted by mippy at 5:33 AM on July 29, 2010 [1 favorite]

I wouldn't read too much into the fact that she gave you her number. It's not really the same as giving your number to a random person you meet at a bar. If I was at a party with my significant other and I gave my number to a person who I know is friends with my S.O., I wouldn't be doing it with the intention of sleeping with or dating that person later, I'd be doing it because I want to be better friends with that person.

Don't approach this girl with your superior stats and proposals like "I'll support you until you find a job" -- it makes you sound like you want to be her sugar daddy.

Wait it out and be a good friend to her. Your romantic relationship will have a more solid foundation if it starts with her making the decision to leave him on her own.posted by neushoorn at 5:38 AM on July 29, 2010 [1 favorite]

It might important ask yourself why is she in this relationship with your friend? She has to be getting something out of this (healthy or not).
I suspect if he really is everything that you describe, she won't be interested in guy that treats her like a princess. Sounds like she may be attracted to jerks. If that's the case, you ought not apply for that position.posted by WhiteWhale at 5:52 AM on July 29, 2010

Thanks, everyone. This guy has openly admitted to sleeping with girls in relationships (to both the girl and his own parents) and that reminds me that I am not him.

I'll just go about my life and be a good friend. There's no sense in worrying about what might happen in the future.posted by BearPaws at 6:02 AM on July 29, 2010 [7 favorites]

Yeah. Speaking as someone who has been the girl, do not do this.posted by millipede at 6:05 AM on July 29, 2010

If she really likes you, tell her that you cannot date her until she's broken up with friend and been single for 2 months.posted by k8t at 6:19 AM on July 29, 2010 [2 favorites]

I agree with Houstonian. Just ask her out.

You don't sound chivalrous, not that chivalry is something that women are looking for anyway. Or 3.0 GPAs. But what the hell.

You're in college and doing this kind of stuff can be what college is all about. From your description you all seem kind of wild. This guy obviously isn't a friend you can't stand to lose. So go for it. But be prepared for the consequences to suck.

I am a woman who did all sorts of stupid things in college I don't regret and this advice is 100% sincere.posted by vincele at 6:20 AM on July 29, 2010

Don't be the nice guy who gets used as a sympathetic ear whenever she needs to complain about her boyfriend and boost her self esteem. You'll just be a pawn in their relationship drama.

Go out, meet girls, date. You'll be
more intetesting for not being always available.posted by Omnomnom at 6:20 AM on July 29, 2010 [2 favorites]

nthing that you can do better and should go meet/date other people.

i think trying to be a good friend will drive you crazy and won't attract her. the "honorable" thing to do, as i see it, would be being honest with the people involved: say you're interested in the girl and so can't be friends with a good conscience. Regardless of your interest, why are you friends with these people when you seem to despise them?

If you flirt via text a bit leading up to some drinks, stuff can happen. That being said, I'd worry that you want this girl right now specifically because you can't have her. Watch out for that.posted by fso at 7:56 AM on July 29, 2010 [1 favorite]

Once upon a time when I was young, stupid and not a very good boyfriend, I came home one day to find my best friend (since we were 9!) and the mother of my child making waves in my waterbed.

It wasn't the worst day of my life. But the next few weeks and months were as my entire circle of friends collapsed. To hang out with me meant they couldn't hang him and so on. It was a nightmare of anxiety and distrust and pain compounded by the rumors and the backstabbing and the whispers. I was heartbroken and mostly friendless. My entire universe had collapsed.

It's been 15+ years now. I've largely forgiven her; because lets be honest - that relationship was circling the drain anyway.

On the other hand, he may have grown up now to be the finest human being the world has ever known. But I'll never know, and I don't care to. Ever. I've never held a grudge, except this one time.

So, to answer your question - wait until the boyfriend goes off to fight forest fires in Northern Minnesota for a couple of weeks and then make your move.

Your best friend, who you despise because he is damaged and inferior to you, has a girlfriend who is equally damaged and inferior but who you respect just enough to want to get into her pants.

She gave you her number and you are interpreting this as an invitation into the pants zone.

The honourable thing to do would be to stop hanging out with these people because you despise them and aren't really their friend.

The neutral thing to do would be to be available and wait.

The really interesting thing to do would be to make a lunge for the girlfriend's pants and then come back and tell us how it went. I look forward to many future questions regarding medical bills, lawsuits, restraining orders, addiction programs, who owes what for debts incurred by your substance-abusing ne'er do well of an ex, GPA damage control, and how hard it will be to get a full-time job out of college considering [insert bad experience laundry list here].

I'm kind of bored with my own life, so I say go for the third thing. I'll just sit here and keep refreshing the page.posted by tel3path at 8:14 AM on July 29, 2010 [42 favorites]

To hang out with me meant they couldn't hang him and so on. It was a nightmare of anxiety and distrust and pain compounded by the rumors and the backstabbing and the whispers.

Are you ready to loose all of the friends who know both you and "best friend?" Lovers tend to come and go, but friends are precious. Never jeopardize a friendship for sex - you'll be very sorry.posted by The Light Fantastic at 8:48 AM on July 29, 2010

I asked a question with comprable drama, about two years ago, and the best advice I got was: When you see a minefield walk around it, not through it. I know this sucks to watch. Sorry man.posted by ShadePlant at 8:52 AM on July 29, 2010 [6 favorites]

Stop hanging out with the boyfriend, in a casual way. When the girl reaches out to find out why, which she will do if she is interested, when she notices you're not showing up to things lately, say "eh, I'm just not all that interested in hanging out with [the boyfriend] any more, I've got other things going on. Kind of a shame, though, because it means I don't get to see you." Move on with your life, without the boyfriend (who you don't like anyway) and without her (because where she goes, the boyfriend goes.)

Then, if she dumps him, and she's still interested, she'll reach out to you and invite you to something. She'll tell you that she and the boyfriend have split up, so you don't have to worry about him being there. THEN and only then should you go for it. Otherwise it's just a world of stupid drama.posted by davejay at 10:10 AM on July 29, 2010 [2 favorites]

tl;dr -- remove the boyfriend from your life, to improve it in the short term, and in the long term if she does the same, there won't be any drama.posted by davejay at 10:11 AM on July 29, 2010

Why are you not going after someone completely available with no accompanying drama? This is a far more important question.posted by Ironmouth at 10:24 AM on July 29, 2010 [3 favorites]

I'm so confused about whose friend is friend is boygirl friend and what best friend isn't best but only friend friend even though you called said friend best. Wait, is the boyfriend your not-best friend? Because at first I was reading your question as trying to date your best friend's daughter. ("WTF") Get your shit together.

Maybe work out what "sustainable connection" and "best friend" actually mean first, and no, Facebook doesn't count at all, if you're into that sort of thing.posted by Ky at 10:55 AM on July 29, 2010

What, the more I think about it, it dawns on me that the fact you can't even distinguish what real friendship is (he's your "best" friend whom you don't want to be around for life?!) bodes ill for your collegiate gerbil sex conquest (no, wait, gerbil sex is the easy part at your age) "sustainable connection" conquest.

If the guy is such a poor relation to hang out with to the extent that you even call him a jerk and are afraid of getting into random violence, and yet you still call him your best friend.... what, are you hoping that everyone you meet will compare you two and you'll always come out on top? Baffling. Why not hang out with, I dunno, some good people first?posted by Ky at 11:07 AM on July 29, 2010

I have never really understood the disdain for being involved in a relationship as the third one. It implies that women are passive individuals incapable of making their own choices and a man courting woman already involved in other relationship is somehow always able to effectively influence woman's decision whether or not she would like to left her current partner for the new one. Simply speaking: women are not objects thus they can not be stolen. And if the third one is honest in such situation he can not seduce her either. So I'd nth the suggestion of Houstonian -- call her up and ask her for a date.

Having said that I must insist that in order to do it ethically you must be sure that you really care about the girl. By caring I don't mean possible future financial support but asking yourself what is the best for her in the long term. You must consider the inevitable fallout of your success and whether or not she wouldn't be better leaving her boyfriend on her own terms when she will be ready for it.

In the film Casablanca both Rick (Bogart) and Victor Laszlo (Reid) were caring about Ilsa (Bergman) to the point of wanting her to leave with the other one. If you care about the girl as they did, by all means, do it. If you don't, don't.posted by przepla at 11:45 AM on July 29, 2010 [1 favorite]

You're barking up the wrong tree bro. "Chivalry" and "treating her right" aren't as persuasive elements as you'd like to think, especially in an introductory phase. She probably digs this guy BECAUSE he treats her offhandishly and BECAUSE he never says those things to her. Her bringing that up in front of you to him was beta-chum for you my friend (sorry to say). If you like her enough, you gotta make a move hard. I'd be open about it with your friend unless you want to sacrifice the friendship for the prospect of the girl. If not, be as dastardly as you think might help, and it seems like you're leaning that way, especially how you're hanging him to dry on this post.

Evil advice, but in a tight spot you make moves...posted by Hurst at 12:00 PM on July 29, 2010

Congrats on identifying the things about a member of the opposite sex you would like to find in a partner. Remember them.

Good relationships involve people you can actually communicate with openly and honestly. This applies to friendships and romantic relationships too. The world is big, and full of people capable of treating each other well. Rise to the challenge. Go meet some of them, and treat them well, and you'll get good results.

In addition, the girl who would leave her bf and be with his friend isn't worth more than few-night fling. WAY too much drama.posted by coolguymichael at 12:36 PM on July 29, 2010 [1 favorite]

I think the previous comments cover pretty well the idea that it would be wise to move on, move away, and realise you really wouldn't want this if it worked out in reality given the cost. But, totally seriously, take a look at the lyrics to the song you used in the title, as a cautionary tale by omission - it's from the point of view of the guy who's the (still smitten) ex, and he doesn't mention anything about the new guy other that who he's dating.posted by carbide at 2:19 PM on July 29, 2010

"kind of a jerk"

"inconsiderate"

"has no idea of chivalry"

"i'm worried that he'll offend someone and get us both into a fight."

"not a friend I would probably want to be around for life"

Those are some interesting things to be saying about a "best friend", dude.

My advice would be to stay the hell away from this. Or ditch your "best friend" and then, maybe, if you really think it's worth it, start thinking about seeing if the girl is interested. Just be ready for ugliness if you take the latter course.posted by Decani at 4:12 PM on July 29, 2010

The only reason I used "My Best Friend's Girl" was due to a reference to a song by The Cars.posted by BearPaws at 4:38 PM on July 29, 2010

I would ask her out. Life's too short.posted by karizma at 9:35 PM on July 29, 2010

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